Carbon Dioxide → HCID 54383158, compound

HRID 1700403Notes

Reaction equation

HRID 1700403 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([CH3:23])=[O:22].C[O-].[Na+].[C:27](=O)=[O:28]>CO>[CH3:27][O:28][C:19]([C:4]1[C:3]([S:21]([CH3:23])=[O:22])=[C:2]([NH2:1])[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=1)=[NH:20]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 10861895HCID 10861895, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 54383158HCID 54383158, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carbonitrile (5.0 g) in anhydrous methanol was added a 25% w/w solution of sodium methoxide (8.95 ml) in methanol, at 20 ° C. The mixture was stirred for 16-hours, cooled to 0° C. and diluted with ice-cold anhydrous methanol. Carbon dioxide was passed into the solution for 15-minutes until a pH of 8 was attained. The precipitate was filtered off, washed (ethyl acetate) and evaporated to give 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboximidic acid methyl ester (3.65 g), 1H NMR (CDCl3) in ppm: 8.34(s,1H), 7.79(s,2H), 5.11(brs,2H), 3.93(s,3H), 2.94(s,3H). By proceeding in a similar manner the following compound was prepared:5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethylsulfinyl-1H-pyrazole-3-carboximidic acid methyl ester, m.p. 179-180 ° C.

Workup

  1. customat 20 ° C
  2. additiondiluted with ice-cold anhydrous methanol
  3. filtrationThe precipitate was filtered off
  4. washwashed (ethyl acetate)
  5. customevaporated

Sources & evidence

ORD record
ord-42b93caaaec1482785f48007801ffcc5
Source dataset
uspto-grants-2002_02
Patent number
US06350771B1

Reaction notes

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